Boron trifluoride etherate → HCID 66977065, compound

HRID 712253Notes

Reaction equation

HRID 712253 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][CH:9]([CH2:12][OH:13])[CH2:10][OH:11])=[N:6][CH:7]=1.[C:14]([O:19][CH2:20][CH3:21])(=[O:18])[C:15]([CH3:17])=O.B(F)(F)F.CCOCC>C(#N)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]([NH:8][CH:9]2[CH2:10][O:11][C:15]([CH3:17])([C:14]([O:19][CH2:20][CH3:21])=[O:18])[O:13][CH2:12]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 12041Ethyl pyruvateHCID 65314437HCID 65314437, compound

Product 1

HCID 66977065HCID 66977065, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[(5-bromopyrimidin-2-yl)amino]propane-1,3-diol (100 mg, 0.40 mmol), ethyl pyruvate (80 μL, 0.72 mmol) and acetonitrile (2 mL) were combined at rt. An aliquot of borontrifluoride etherate (100 μL, 0.80 mmol) was added to the reaction mixture and stirring was continued at rt for 24 hrs. A further portion of borontrifluoride etherate (100 μL, 0.80 mmol) was added to the reaction mixture, which was stirred at rt for a further 24 hrs. The reaction mixture was loaded directly onto a column for flash chromatography (12 g silica column), eluting with 0-100% EtOAc gradient in n-heptane, to give desired product (105 mg, light brown oil). m/z 345.9/347.9 [M+H]+.

Workup

  1. customwere combined at rt
  2. stirringwas stirred at rt for a further 24 hrs
  3. washeluting with 0-100% EtOAc gradient in n-heptane

Sources & evidence

ORD record
ord-a1e04cdd44814005820f3f7001e616cb
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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